So I just had this idea: I have read that DMT freebase prepared from thermal decomposition of the acetate has been successfully recrystallised in naphtha. Now, the boiling point of acetic acid is 118 to 119 °C; 244 to 246 °F; 391 to 392 K; surely if one were to heat the DMT acetate in higher boiling naphtha, e.g. >140 °C, the acetic acid would boil off and the naphtha could then be cooled judiciously to obtain (one would hope) some nice white crystals of freebase?

Some examples are the boiling point of octane is 125.1 to 126.1 °C (257.1 to 258.9 °F; 398.2 to 399.2 K), that of nonane 150.4 to 151.0 °C (302.6 to 303.7 °F; 423.5 to 424.1 K) and decane, 173.8 to 174.4 °C (344.7 to 345.8 °F; 446.9 to 447.5 K). One would have to use a fractionating column to achieve successful separation of the acetic acid which kind of defies the point of the acetate decomposition method a bit. It might be a fun experiment, though.

Overall, it's probably better to just heat the DMT acetate in plenty of water, the more volatile acetic acid will distil out with the water.

So why should this latter process work? DMT and acetic acid are both moderately weak in their respective basicity and acidity. This means that in solution, DMT acetate is always partly decomposed into acetic acid and DMT freebase. (The equilibrium for this can be worked out using pKa and pKb values.)

In a way it's fortunate here that DMT freebase is not steam-volatile, even if some had hoped that the steam distillation of DMT might be a viable process.

Distilling out acetic acid from the solution causes an equilibrium to be re-established, forming more acetic acid from the acetate ions. This will distil out until there is virtually no acetic acid left and DMT freebase and water remain in the flask (if it hasn't boiled dry, I suppose), perhaps in solution, as an emulsion or an oily layer on top. Then all that remains is to collect the freebase.

Is anyone doing any of this already? Or have we possibly concluded that it's simply not effective or worthwhile?